Nikel-Catalyzed Enantioselective C(sp            3)-H Arylation of Ketones with Aryl Ethers via Selective C            Ar-O Cleavage to Construct All-Carbon Quaternary Stereocenters

Mingliang Li; Jun Joelle Wang

doi:10.31635/ccschem.022.202101611

Nikel-Catalyzed Enantioselective C(sp ³)-H Arylation of Ketones with Aryl Ethers via Selective C _Ar-O Cleavage to Construct All-Carbon Quaternary Stereocenters

Mingliang Li
, Jun Joelle Wang^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

4 Citations (Scopus)

Abstract

We designed thenickel-catalyzed enantioselective C(sp³)-H arylation of ketones with phenol-derived aryl pyrimidyl ethers via selective cleavage of the C(aryl)-O bond to construct all-carbon quaternary stereocenters. This method exhibits good functional group compatibility and broad substrate scope. Drug molecule donepezil can directly transform into corresponding highly optically pure derivatives with this developedmethodology. Mechanistic studies reveal that C(aryl)-O cleavage of aryl pyrimidyl ether probably proceeded by means of an anionic organo-Ni(0) intermediate.

Original language	English
Pages (from-to)	2921-2929
Number of pages	9
Journal	CCS Chemistry
Volume	4
Issue number	9
DOIs	https://doi.org/10.31635/ccschem.022.202101611
Publication status	Published - 5 Sept 2022

User-Defined Keywords

all-carbon quaternary stereocenter
aryl pyrimidyl ether
asymmetric arylation
C-O cleavage
Nickel catalysis

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10.31635/ccschem.022.202101611

Cite this

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title = "Nikel-Catalyzed Enantioselective C(sp 3)-H Arylation of Ketones with Aryl Ethers via Selective C Ar-O Cleavage to Construct All-Carbon Quaternary Stereocenters",

abstract = "We designed thenickel-catalyzed enantioselective C(sp3)-H arylation of ketones with phenol-derived aryl pyrimidyl ethers via selective cleavage of the C(aryl)-O bond to construct all-carbon quaternary stereocenters. This method exhibits good functional group compatibility and broad substrate scope. Drug molecule donepezil can directly transform into corresponding highly optically pure derivatives with this developedmethodology. Mechanistic studies reveal that C(aryl)-O cleavage of aryl pyrimidyl ether probably proceeded by means of an anionic organo-Ni(0) intermediate.",

keywords = "all-carbon quaternary stereocenter, aryl pyrimidyl ether, asymmetric arylation, C-O cleavage, Nickel catalysis",

author = "Mingliang Li and Wang, \{Jun Joelle\}",

note = "Funding Information: We gratefully acknowledge the National Natural Science Foundation of China (no. NSFC 21902072) and the Guangdong Innovative Program (no. 2019BT02Y335) for their financial support. Publisher Copyright: {\textcopyright} Journal of Gastrointestinal Oncology. All rights reserved.",

year = "2022",

month = sep,

day = "5",

doi = "10.31635/ccschem.022.202101611",

language = "English",

volume = "4",

pages = "2921--2929",

journal = "CCS Chemistry",

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publisher = "Chinese Chemical Society",

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T1 - Nikel-Catalyzed Enantioselective C(sp 3)-H Arylation of Ketones with Aryl Ethers via Selective C Ar-O Cleavage to Construct All-Carbon Quaternary Stereocenters

AU - Li, Mingliang

AU - Wang, Jun Joelle

N1 - Funding Information: We gratefully acknowledge the National Natural Science Foundation of China (no. NSFC 21902072) and the Guangdong Innovative Program (no. 2019BT02Y335) for their financial support. Publisher Copyright: © Journal of Gastrointestinal Oncology. All rights reserved.

PY - 2022/9/5

Y1 - 2022/9/5

N2 - We designed thenickel-catalyzed enantioselective C(sp3)-H arylation of ketones with phenol-derived aryl pyrimidyl ethers via selective cleavage of the C(aryl)-O bond to construct all-carbon quaternary stereocenters. This method exhibits good functional group compatibility and broad substrate scope. Drug molecule donepezil can directly transform into corresponding highly optically pure derivatives with this developedmethodology. Mechanistic studies reveal that C(aryl)-O cleavage of aryl pyrimidyl ether probably proceeded by means of an anionic organo-Ni(0) intermediate.

AB - We designed thenickel-catalyzed enantioselective C(sp3)-H arylation of ketones with phenol-derived aryl pyrimidyl ethers via selective cleavage of the C(aryl)-O bond to construct all-carbon quaternary stereocenters. This method exhibits good functional group compatibility and broad substrate scope. Drug molecule donepezil can directly transform into corresponding highly optically pure derivatives with this developedmethodology. Mechanistic studies reveal that C(aryl)-O cleavage of aryl pyrimidyl ether probably proceeded by means of an anionic organo-Ni(0) intermediate.

KW - all-carbon quaternary stereocenter

KW - aryl pyrimidyl ether

KW - asymmetric arylation

KW - C-O cleavage

KW - Nickel catalysis

UR - https://www.scopus.com/pages/publications/85137915742

U2 - 10.31635/ccschem.022.202101611

DO - 10.31635/ccschem.022.202101611

M3 - Journal article

SN - 2096-5745

VL - 4

SP - 2921

EP - 2929

JO - CCS Chemistry

JF - CCS Chemistry

IS - 9

ER -

Nikel-Catalyzed Enantioselective C(sp ³)-H Arylation of Ketones with Aryl Ethers via Selective C _Ar-O Cleavage to Construct All-Carbon Quaternary Stereocenters

Abstract

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